616202-81-4

Basic information

• Product Name: 1H-3-Benzazepine, 8-chloro-2,3,4,5-tetrahydro-1-Methyl-, (1S)-
• Synonyms: 1H-3-Benzazepine, 8-chloro-2,3,4,5-tetrahydro-1-Methyl-, (1S)-;(S)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine;Lorcaserin Impurity 2
• CAS NO: 616202-81-4
• Molecular Formula: C₁₁H₁₄ClN
• Molecular Weight: 195.68856
• EINECS: 1312995-182-4
• Mol File: 616202-81-4.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-3-Benzazepine, 8-chloro-2,3,4,5-tetrahydro-1-Methyl-, (1S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-3-Benzazepine, 8-chloro-2,3,4,5-tetrahydro-1-Methyl-, (1S)-(616202-81-4)
• EPA Substance Registry System: 1H-3-Benzazepine, 8-chloro-2,3,4,5-tetrahydro-1-Methyl-, (1S)-(616202-81-4)

Safety Data

• Hazardous Substances Data: 616202-81-4(Hazardous Substances Data)

Usage

General Description

1H-3-Benzazepine, 8-chloro-2,3,4,5-tetrahydro-1-methyl-, (1S)- is a chemical compound with a complex structure. It belongs to the class of benzazepines and contains a chloro group as well as a methyl group. The (1S)- designation indicates the stereochemistry of the molecule, meaning that it has a specific arrangement of atoms in space. 1H-3-Benzazepine, 8-chloro-2,3,4,5-tetrahydro-1-methyl-, (1S)- may have potential pharmacological properties, as benzazepines are known to have diverse biological activities, including as antipsychotic and anticonvulsant agents. The chloro and methyl groups could contribute to its specific pharmacological effects. Overall, this compound has potential significance in pharmaceutical research and development.

Upstream product

• 616201-80-0 (+/-)-Lorcaserin 
• 34164-14-2 N-(4-chlorophenylethyl)-2-chloropropanamide 
• 156-41-2 4-chlorophenylethylamine 
• 824430-77-5 8-chloro-1-methyl-4,5-dihydro-1H-benzo[d]azepin-2(3H)-one 
• 616202-78-9 (1S)-N-trifluoroacetyl-8-chloro-2,3,4,5-tetrahydro-1-methyl-1H-3-benzazepine 

Downstream Products

• 851477-54-8 (S)-N-tert-butoxycarbonyl-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine 
• 851477-71-9 (S)-N-trifluoroacetyl-8-chloro-7-iodo-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine 
• 824430-78-6 (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine L-(+)-tartrate 
• 846589-98-8 Lorcaserin hydrochloride 
• 616201-80-0 (+/-)-Lorcaserin 

Relevant articles and documents

Synthesis of 3-Benzazepines by Metal-Free Oxidative C–H Bond Functionalization–Ring Expansion Tandem Reaction

A metal-free synthesis of biologically important benzazepines is achieved through a single synthetic operation involving an oxidative C–H bond functionalization and ring expansion with diazomethanes as key reagent. This represents a new, strong methodology for the straightforward construction of the seven-ring N-heterocyclic structures under mild conditions using a 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO) oxoammonium salt as oxidant. Moderate to good yields are achieved from simple, readily available tetrahydroisoquinolines, and this methodology has been further successfully applied for the synthesis of the 3-benzazepine drug Lorcaserin. A possible mechanistic pathway for the ring expansion step, comprising the extrusion of nitrogen in a concerted asynchronic process, is proposed based on both mechanistic proof and density function theory (DFT) calculations. (Figure presented.).

Discovery and SAR of new benzazepines as potent and selective 5-HT 2C receptor agonists for the treatment of obesity

We report on the synthesis, biological evaluation and structure-activity relationships for a series of 3-benzazepine derivatives as 5-HT2C receptor agonists. The compounds were evaluated in functional assays measuring [3H] phosphoinositol turnover in HEK-293 cells transiently transfected with h5-HT2C, h5-HT2A or h5-HT2B receptors. Several compounds are shown to be potent and selective 5-HT 2C receptor agonists, which decrease food intake in a rat feeding model.

BENZAZEPINE DERIVATIVES AND METHODS OF PROPHYLAXIS OR TREATMENT OF 5HT2C RECEPTOR ASSOCIATED DISEASES

The present invention relates to substituted-2,3,4,5-tetrahydro-3-benzazepine derivatives that are modulators of the 5HT2C receptor. Accordingly, compounds of the present invention are useful for the prophylaxis treatment of 5HT2C receptor associated diseases, conditions or disorders, such as, obesity and related disorders.